Nora O’Connor is a super collaborator, someone who loves singing harmonies and makes everyone sound good. She’s a member of the Chicago all-star group the Flat Five and a formidable singer-songwriter in her own right, as her 2022 solo album, My Heart, her first in 18 years, reminded us. Here she reflects on her life as “a music worker,” including what she’s learned from performing with such artists as the Decemberists, Iron & Wine, Mavis Staples, Andrew Bird, the New Pornographers and Neko Case. How has she has balanced her career and family life—and would a male performer have faced similar challenges? What ambitions does she have for herself and the Flat Five? What's the secret behind the alchemy she creates with frequent collaborator/Flat Five bandmate Kelly Hogan? And what role has the Chicago club the Hideout played in her musical life?